Study of DNA interactions with cyclic chalcone derivatives by spectroscopic techniques

Štefanišinová, Miroslava; Tomečková, Vladimı́ra; Kožurková, Mária; Ostró, A; Mareková, Mária

doi:10.1016/j.saa.2011.06.071

Cited by 18 publications

(12 citation statements)

References 29 publications

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“…In the K1-MeOH, we noticed a considerable charge transfer ca. 16.71 kcal mol −1 from lp(1)n C=O and 18.23 kcal mol −1 from lp(2)n C=O to σ* O-H of the alcohol molecule. This is to be compared to only 3.80 kcal mol −1 conjugation in the K1-ACN complex.…”

Section: Structural and Electronic Features At The Ground Statementioning

confidence: 99%

“…This interaction is possible by two means: i) through dipole-dipole interaction, due to C=O polarization, or ii) via hydrogen bonding (H-bonding) that involves the two lone-pair electrons of the oxygen sp 2 hybridized orbital [15]. Moreover, recent studies based on fluorescence spectroscopy showed that cycloalkanones bind to BSA protein and DNA and the outcome of this interaction depends on their concentration [16,17].…”

Section: Introductionmentioning

confidence: 99%

“…Our interest in these important biologically active cycloalkanones came due to the fact that the complete mechanism for their interaction with DNA and protein is still not completely understood [16,17]. Thus, in this work, we continue our investigation on one of the cycloalkanones we previously synthesized [18].…”

Section: Introductionmentioning

confidence: 99%

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The electronic origin of the ground state spectral features and excited state deactivation in cycloalkanones: the role of intermolecular H-bonding in neat and binary mixtures of solvents

Al‐Ansari

2019

J Mol Model

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In this study, a D-A cycloalkanone (K1) has been investigated by steady state absorption and fluorescence in neat solvents and in three binary mixtures of nonpolar aprotic/polar protic, polar aprotic/polar protic, and polar protic/polar protic solvents. The experimental findings were complemented by density functional theory (DFT), time-dependent density functional theory (TD-DFT), and NBO quantum-mechanical calculations. Experimentally, effective changes in absorption and fluorescence were observed by solute-solvent interaction. The binary K1-solvent 1-solv 2 configuration, modeled at the B3LYP-DFT level, confirms involvement of inter-molecular H-bonding with the carbonyl C=O in the fluorescence deactivation process (quenching). This is supported by considerable electron delocalization from C=O to the solvent's hydroxyl (n O → σ* H-O). This type of hyperconjugation was found to be the main driver for solute-solvent stabilization.

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Section: Structural and Electronic Features At The Ground Statementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The electronic origin of the ground state spectral features and excited state deactivation in cycloalkanones: the role of intermolecular H-bonding in neat and binary mixtures of solvents

Al‐Ansari

2019

J Mol Model

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“…Stefansinova et al . working on the same cyclic chalcones, found that the absorption increased and exhibited significant red shift when binding to ctDNA.…”

Section: Introductionmentioning

confidence: 95%

Synthesis, Vibrational (IR), Thermal analysis and Quantumchemical Study of a Series of Cyclic Chalcones

Al‐Ansari

2016

ChemistrySelect

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In this work, the influence of expanding the cyclic ring (adding methylene group) on the properties of three dimethylamino chalcones derivatives (1-3), is addressed, using a combined experimental (vibrational spectra (IR), Differential scanning calorimetry (DSC) and thermo-gravimetric analysis (TGA) and theoretical (density functional theory (DFT) and natural bond order (NBO) techniques.Based on our DFT calculations, these molecules, have two structurally stable conformers a and b, where the later predominates at room temperature. A comparison of the experimental data and theoretical structure energies results, show that rotamer a transforms to b prior to melting.The formation of intramolecular hydrogen bond in these molecules, has been demonstrated by B3LYP/6-31 + +G(d,p) calculation and the natural bond orbital method (NBO). The influence of expanding the cyclic ring on the donor (dimethylanilino group) and the acceptor (benzoyl motif) interaction is addressed. Additionally, the structural influence on the CH···O= C stabilization energies is discussed.Further, it was found that CÀH group acts as a proton donor leading to a red shift in the carbonyl n C = O stretching mode.[a] Dr.

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“…Much effort has also been directed to study DNA-small molecule interactions, such as the interaction with inorganic complexes [5,8,9], fluorescent dyes [10,11] and most importantly organic molecules [12][13][14][15][16][17]. These studies help to understand the molecular basis of complex diseases and may provide potential drug candidates.…”

Section: Introductionmentioning

confidence: 99%

Novel cholinesterase modulators and their ability to interact with DNA

Janočková¹,

Gulasova²,

Musílek

et al. 2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Study of DNA interactions with cyclic chalcone derivatives by spectroscopic techniques

Cited by 18 publications

References 29 publications

The electronic origin of the ground state spectral features and excited state deactivation in cycloalkanones: the role of intermolecular H-bonding in neat and binary mixtures of solvents

The electronic origin of the ground state spectral features and excited state deactivation in cycloalkanones: the role of intermolecular H-bonding in neat and binary mixtures of solvents

Synthesis, Vibrational (IR), Thermal analysis and Quantumchemical Study of a Series of Cyclic Chalcones

Novel cholinesterase modulators and their ability to interact with DNA

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